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Search for "intramolecular cyclization" in Full Text gives 259 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Formaldehyde surrogates in multicomponent reactions

  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Bernhard Westermann

Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45

Graphical Abstract
  • peptide carbonyl group. Both moieties result from the glyoxylate compound (Scheme 43). There are many examples in which the ester moiety opens the possibility of a further intramolecular cyclization with a nucleophile (for example, a protected amine in an Ugi/deprotection/cyclization sequence [98][99][100
  • proton in the C-α position, which leads to a stable carbanion with even mild bases, that can promote intramolecular cyclization. For example, Flores-Constante et al. [106] and Nechaev et al. [107] synthesized Ugi adducts with a propargyl group that could be used as a Michael acceptor (48–50, Scheme 44
  • radical species of the ammonium persulfate salt. Subsequently, the radical delocalization process gives rise to the carbon-centered radical, which follows the intramolecular cyclization onto the double bond or onto the aromatic ring depending on the case. The γ-lactams 56 and isoindolinones 57 can
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Published 13 Mar 2025

Synthesis of electrophile-tethered preQ1 analogs for covalent attachment to preQ1 RNA

  • Laurin Flemmich and
  • Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 483–489, doi:10.3762/bjoc.21.35

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  • were required to obtain the corresponding mesylate 3b. Similar to 11, compound 12 was isolated as its trifluoroacetate salt. Selective Boc protection of the aliphatic amine gave 13, which was selectively O-mesylated to give compound 14. Compound 14 was found to slowly undergo intramolecular cyclization
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Published 04 Mar 2025

New tandem Ugi/intramolecular Diels–Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives

  • Yuriy I. Horak,
  • Roman Z. Lytvyn,
  • Andrii R. Vakhula,
  • Yuriy V. Homza,
  • Nazariy T. Pokhodylo and
  • Mykola D. Obushak

Beilstein J. Org. Chem. 2025, 21, 444–450, doi:10.3762/bjoc.21.31

Graphical Abstract
  • under the Ugi reaction conditions (Scheme 1). A furan double bond and an exocyclic double bond, forming the diene, enter the intramolecular cyclization, and a residue formed by the monoanilide of maleic acid acts as a dienophile. Notably, non-cyclized Ugi adducts A1 were not found in the products. The
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Published 26 Feb 2025

Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones

  • Yurii A. Sayapin,
  • Eugeny A. Gusakov,
  • Inna O. Tupaeva,
  • Alexander D. Dubonosov,
  • Igor V. Dorogan,
  • Valery V. Tkachev,
  • Anna S. Goncharova,
  • Gennady V. Shilov,
  • Natalia S. Kuznetsova,
  • Svetlana Y. Filippova,
  • Tatyana A. Krasnikova,
  • Yanis A. Boumber,
  • Alexey Y. Maksimov,
  • Sergey M. Aldoshin and
  • Vladimir I. Minkin

Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26

Graphical Abstract
  • reactions of 2-methylquinolines with 3,5-di-(tert-butyl)-1,2-benzoquinone [1] and benzophenones with o-chloranil [15]. The norcaradiene derivatives 5, formed in the next step by the intramolecular cyclization reaction of 4, undergo thermal isomerization into 2,3-dihydrotropolones 6. The formation of 2
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Published 17 Feb 2025

Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles

  • Yujun Pang,
  • Jinglan Yan,
  • Nawaf Al-Maharik,
  • Qian Zhang,
  • Zeguo Fang and
  • Dong Li

Beilstein J. Org. Chem. 2025, 21, 234–241, doi:10.3762/bjoc.21.15

Graphical Abstract
  • abstraction to yield the hydrodifluoromethylation product. Building upon this work, we hypothesized that if the newly formed alkyl radical could undergo intramolecular cyclization with an aromatic ring, instead of hydrogen abstraction, it could enable the construction of polycyclic structures. Thus, as part
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Published 30 Jan 2025

Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization

  • Asahi Kanno,
  • Ryo Tanifuji,
  • Satoshi Yoshida,
  • Sota Sato,
  • Saori Maki-Yonekura,
  • Kiyofumi Takaba,
  • Jungmin Kang,
  • Kensuke Tono,
  • Koji Yonekura and
  • Hiroki Oguri

Beilstein J. Org. Chem. 2025, 21, 226–233, doi:10.3762/bjoc.21.14

Graphical Abstract
  • coupling of alkyne 8, THIQ segment 9, and benzaldehyde would enable convergent assembly of the building blocks to produce 10 [43][44][45][46]. Removal of the cyclic acetal in 10 followed by Strecker-type conversion leading to an α-amino nitrile would enable tandem intramolecular cyclization with phenol to
  • transformations: copper(I)-catalyzed regiocontrolled three-component assembly of alkyne 8, THIQ segment 9, and benzaldehyde to yield 10, followed by tandem Strecker reaction and intramolecular cyclization to form 2,3-diaminobenzofuran 11. Subsequent gold(I)-mediated 6-endo hydroamination of 11 leads to the
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Published 28 Jan 2025

Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations

  • Seungmin Lee,
  • Minsuk Kim,
  • Hyewon Han and
  • Jongwoo Son

Beilstein J. Org. Chem. 2025, 21, 200–216, doi:10.3762/bjoc.21.12

Graphical Abstract
  • ) nitrenoid intermediate INT-7. Subsequent nitrene insertion, protodemetalation, and intramolecular cyclization furnish the desired 1,2,4-triazole. 1.3 Three-component formation of N-acyl amidines In 2019, N-acyl amidines were prepared from dioxazolones using a copper catalyst with terminal alkynes and
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Published 22 Jan 2025

Recent advances in electrochemical copper catalysis for modern organic synthesis

  • Yemin Kim and
  • Won Jun Jang

Beilstein J. Org. Chem. 2025, 21, 155–178, doi:10.3762/bjoc.21.9

Graphical Abstract
  • elimination, produces C–H alkynylated arene 10, which then forms the final product 3 through intramolecular cyclization. Finally, the Cu(I) complex 9 produced via reductive elimination is reoxidized at the anode to regenerate the Cu(II) complex 4, completing the catalytic cycle. Yao and Shi developed the
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Published 16 Jan 2025

Recent advances in organocatalytic atroposelective reactions

  • Henrich Szabados and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

Graphical Abstract
  • reaction pathway was proposed [56]. The first step is a CPA C27-catalyzed condensation giving rise to the imine intermediate followed by isomerization to the enamine stabilized by CPA. An enantioselective intramolecular cyclization followed by dehydration then afford the aromatic ring and desired product
  • . Transition-state calculations gave insight into possible reaction pathways. CPA C48-activated substrates react and rearomatization of the benzene ring leads to the intermediate Int-66. In the presence of an oxidant, axially chiral product 213 is formed. Otherwise, nitrogen-initiated intramolecular
  • cyclization takes place, subsequent β-H elimination, and C–N-bond cleavage lead to the axially chiral indolylaniline 212. Heterobiaryl aldehydes 217a–o and aminobenzamides 218a–g reacted in the presence of CPA C50 leading to axially chiral products 219 (Scheme 64) [94]. Investigating various combinations of
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Published 09 Jan 2025

Non-covalent organocatalyzed enantioselective cyclization reactions of α,β-unsaturated imines

  • Sergio Torres-Oya and
  • Mercedes Zurro

Beilstein J. Org. Chem. 2024, 20, 3221–3255, doi:10.3762/bjoc.20.268

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  • the bifunctional squaramide enables a stereoselective Michael addition of the azlactone to the azadiene forming intermediate A which transforms into intermediate B, which then undergoes an intramolecular cyclization to give the desired product 20. In 2020, Ni, Song and co-workers described a
  • hydrazone intermediate A is formed, which tautomerizes to the enamine B. Finally, this intermediate undergoes an intramolecular cyclization to yield the desired product. Besides, to show the synthetic applicability of the pyrroloindoline derivatives, various transformations were performed (Scheme 21
  • ). Firstly, hydrogenation with palladium on carbon led to the formation of 55 in a good yield. Secondly, an alkylation of the NH of the indole followed by intramolecular cyclization led to tetracyclic derivative 56 in an 80% yield. Next, a deprotection of the azo nitrogen atom led to derivative 57 in a 92
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Published 10 Dec 2024

Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold

  • Thierry Milcent,
  • Pascal Retailleau,
  • Benoit Crousse and
  • Sandrine Ongeri

Beilstein J. Org. Chem. 2024, 20, 3174–3181, doi:10.3762/bjoc.20.262

Graphical Abstract
  • ,anti. Then, hydrazones 3 were reacted with zinc and methyl 2-(bromomethyl)acrylate (4). This aza-Barbier reaction was performed in a biphasic medium (THF/aqueous solution of saturated NH4Cl) to avoid the formation of the α-methylene-γ-lactam obtained by intramolecular cyclization of the zinc amide on
  • . Allylation of fluorinated hydrazones 3a–f to obtain 5a–f. Oxidation of hydrazines 5a–f to obtain hydrazones 6a–f. Intramolecular cyclization of compounds 6a–f to obtain tetrahydropyridazines 7a–f. Preparation of tripeptides 8e, 8e’, 8f, and 8f’. Yields refer to the yield over 2 steps. Supporting Information
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Published 04 Dec 2024

Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies

  • Lucía Campos-Prieto,
  • Aitor García-Rey,
  • Eddy Sotelo and
  • Ana Mallo-Abreu

Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261

Graphical Abstract
  • a multicomponent reaction to obtain SIRT2 inhibitors (Scheme 12). The authors suggest a Knoevenagel condensation approach between isatin derivatives and ethyl cyanoacetate, followed by a Michael addition with C–H activated carbonyl compounds and intramolecular cyclization [50]. They synthesized 45
  • eliminated through microwave-assisted treatment under acidic conditions, resulting in the intramolecular cyclization of the amine onto the ketone derived from glyoxaldehyde (Scheme 14). Vézina-Dawod and co-workers [60] introduced a strategy, which consists of two reactions, for synthesizing highly
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Published 03 Dec 2024

Synthesis of the 1,5-disubstituted tetrazole-methanesulfonylindole hybrid system via high-order multicomponent reaction

  • Cesia M. Aguilar-Morales,
  • América A. Frías-López,
  • Nadia V. Emilio-Velázquez,
  • Alejandro Islas-Jácome,
  • Angelica Judith Granados-López,
  • Jorge Gustavo Araujo-Huitrado,
  • Yamilé López-Hernández,
  • Hiram Hernández-López,
  • Luis Chacón-García,
  • Jesús Adrián López and
  • Carlos J. Cortés-García

Beilstein J. Org. Chem. 2024, 20, 3077–3084, doi:10.3762/bjoc.20.256

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  • , an intramolecular cyclization takes place, facilitated by CuI. This step involves a 5-endo-dig cyclization, where the negatively nitrogen atom of the sulfonamide 25 attacks intramolecularly to yield the intermediate 26. The final product is formed when iodide is regenerated as CuI, allowing it to re
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Published 26 Nov 2024

Advances in radical peroxidation with hydroperoxides

  • Oleg V. Bityukov,
  • Pavel Yu. Serdyuchenko,
  • Andrey S. Kirillov,
  • Gennady I. Nikishin,
  • Vera A. Vil’ and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2024, 20, 2959–3006, doi:10.3762/bjoc.20.249

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Published 18 Nov 2024

Synthesis and antimycotic activity of new derivatives of imidazo[1,2-a]pyrimidines

  • Dmitriy Yu. Vandyshev,
  • Daria A. Mangusheva,
  • Khidmet S. Shikhaliev,
  • Kirill A. Scherbakov,
  • Oleg N. Burov,
  • Alexander D. Zagrebaev,
  • Tatiana N. Khmelevskaya,
  • Alexey S. Trenin and
  • Fedor I. Zubkov

Beilstein J. Org. Chem. 2024, 20, 2806–2817, doi:10.3762/bjoc.20.236

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  • intramolecular cyclization were observed (Table 1, entries 3 and 4). The best results were obtained when isopropyl alcohol was used, which furnished yields of the final product 4а up to 89% within 1 h (entry 9 in Table 1). In the case of methanol and ethanol, the maximum conversion was also observed during the
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Published 05 Nov 2024

Copper-catalyzed yne-allylic substitutions: concept and recent developments

  • Shuang Yang and
  • Xinqiang Fang

Beilstein J. Org. Chem. 2024, 20, 2739–2775, doi:10.3762/bjoc.20.232

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  • yne-allylic cation intermediate, followed by an intramolecular cyclization. The disparity in reactivity could stem from the chelation between acyclic 1,3-dicarbonyl enolates and the copper catalyst, enhancing γ-position attack in an intramolecular manner. Conversely, Meldrum's acid's rigid cyclic
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Published 31 Oct 2024

Base-promoted cascade recyclization of allomaltol derivatives containing an amide fragment into substituted 3-(1-hydroxyethylidene)tetronic acids

  • Andrey N. Komogortsev,
  • Constantine V. Milyutin and
  • Boris V. Lichitsky

Beilstein J. Org. Chem. 2024, 20, 2585–2591, doi:10.3762/bjoc.20.217

Graphical Abstract
  • deprotonates to the anion B under action of DBU. Subsequent intramolecular cyclization at the double bond of pyranone fragment leads to the formation of spiro compound C. Next, opening of the dihydropyranone ring results in pyrrolidin-2-one D which further transformed to the salt of 3-acyltetronic acid E
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Published 14 Oct 2024

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

  • Nian Li,
  • Ruzal Sitdikov,
  • Ajit Prabhakar Kale,
  • Joost Steverlynck,
  • Bo Li and
  • Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

Graphical Abstract
  • cross-coupling between these two intermediates, followed by intramolecular cyclization and subsequent deprotonation results in the desired product (Scheme 20). Furthermore, Budny and coworkers demonstrated that (±)-triticonazole and related compounds could be cyclized and alkoxylated to the
  • that dimerize to form iodine (I2). Subsequent anodic oxidation of in-situ formed Et3N produced an α-amino radical. The iodine then reacts with the alkene to form an iodonium intermediate, which undergoes intramolecular cyclization with losing an electron, and a second water attack to yield the desired
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Published 09 Oct 2024

Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams

  • Valentina Giraldi,
  • Giandomenico Magagnano,
  • Daria Giacomini,
  • Pier Giorgio Cozzi and
  • Andrea Gualandi

Beilstein J. Org. Chem. 2024, 20, 2461–2468, doi:10.3762/bjoc.20.210

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  • /cis dr was determined by 1H NMR analysis of the crude reaction mixture. Intramolecular cyclization of β-lactams induced by photoredox conditions.a Supporting Information Supporting Information File 122: Reaction optimization studies, general experimental procedures, product isolation and
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Published 01 Oct 2024

Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

  • Akiya Ogawa and
  • Yuki Yamamoto

Beilstein J. Org. Chem. 2024, 20, 2114–2128, doi:10.3762/bjoc.20.182

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  • compounds to isocyanides using imidoyl radicals as key intermediates. However, as the number of substituents on typical elements increases, intermolecular 1,1-addition reactions become more difficult due to the increase in steric hindrance. Therefore, it is expected that intramolecular cyclization of
  • with alkenyl, alkynyl, aryl, and isocyano groups as unsaturated groups. Intramolecular cyclization of ortho-alkynylaryl- or ortho-alkenylaryl isocyanides Fukuyama et al. reported that the reaction of an aryl isocyanide with an alkenyl group at the ortho-position with tin hydride in the presence of AIBN
  • Chatani et al. reported that a carbon radical generated by the reaction of RB(OH)2 with Mn(acac)3, added to isocyano groups, is leading to intramolecular cyclization with an ortho-aryl group. The formed aryl radical is oxidized by Mn(acac)3 to convert into an aryl cation, which can be deprotonated to
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Published 26 Aug 2024

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

  • Ignaz Betcke,
  • Alissa C. Götzinger,
  • Maryna M. Kornet and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

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Published 16 Aug 2024

Development of a flow photochemical process for a π-Lewis acidic metal-catalyzed cyclization/radical addition sequence: in situ-generated 2-benzopyrylium as photoredox catalyst and reactive intermediate

  • Masahiro Terada,
  • Zen Iwasaki,
  • Ryohei Yazaki,
  • Shigenobu Umemiya and
  • Jun Kikuchi

Beilstein J. Org. Chem. 2024, 20, 1973–1980, doi:10.3762/bjoc.20.173

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  • generated in the flow reaction system through the intramolecular cyclization of ortho-carbonyl alkynylbenzene derivatives by the π-Lewis acidic metal catalyst AgNTf2 and the subsequent proto-demetalation with trifluoroacetic acid. The 2-benzopyrylium intermediates underwent further photoreactions with
  • intramolecular cyclization followed by proto-demetalation with trifluoroacetic acid (TFA). In catalytic cycle II, photoexcitation of the generated 2-benzopyrylium intermediates A under light irradiation facilitates single-electron transfer (SET) from benzyltrimethylsilane derivatives 2 as the donor molecule
  • intramolecular cyclization of ortho-carbonyl alkynylbenzene derivatives and subsequent proto-demetalation with TFA. Further photoreactions of 2-benzopyrylium intermediates with benzyltrimethylsilane derivatives as the donor molecule were conducted in the flow photoreactor. We confirmed that the flow reaction
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Published 13 Aug 2024

Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA

  • Ze-Nan Hu,
  • Yan-Hui Wang,
  • Jia-Bing Wu,
  • Ze Chen,
  • Dou Hong and
  • Chi Zhang

Beilstein J. Org. Chem. 2024, 20, 1914–1921, doi:10.3762/bjoc.20.167

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  • intramolecular cyclization cascade with excellent chemoselectivity in aqueous CH3CN [25]. Herein, as part of our continuing studies of heterocyclic scaffold synthesis mediated by hypervalent iodine reagents, we present the solvent-dependent chemoselective synthesis of a series of isoquinolinones mediated by PISA
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Published 07 Aug 2024

Novel oxidative routes to N-arylpyridoindazolium salts

  • Oleg A. Levitskiy,
  • Yuri K. Grishin and
  • Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2024, 20, 1906–1913, doi:10.3762/bjoc.20.166

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  • intermediate (i.e., the diarylamines’ radical cation) and indicates the dominance of the intramolecular cyclization over the intermolecular C–N coupling process. Oxidation of diarylamines in the presence of an excess of trifluoroacetic acid gave no targeted pyridoindazolium salts, whereas the amount of
  • diaryldihydrophenazine was increased (10%). Thus, protonation completely suppressed the intramolecular cyclization route. Heterocyclic salts S1–S3 were obtained as amorphous solids, soluble in polar solvents (acetonitrile, DMF, acetone) and chlorinated hydrocarbons (CHCl3, CH2Cl2). The structure of new N
  • exhibit significant bioactivity [4] and can be used as intercalating agents [7]. The very limited scope of these practically useful compounds is mainly attributed to the lack of convenient synthetic approaches to them. Thus, the only example of N-arylpyridoindazolium salts was obtained via intramolecular
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Published 07 Aug 2024

Access to 2-oxoazetidine-3-carboxylic acid derivatives via thermal microwave-assisted Wolff rearrangement of 3-diazotetramic acids in the presence of nucleophiles

  • Ivan Lyutin,
  • Vasilisa Krivovicheva,
  • Grigory Kantin and
  • Dmitry Dar’in

Beilstein J. Org. Chem. 2024, 20, 1894–1899, doi:10.3762/bjoc.20.164

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  • reported in the literature are based on the construction of the β-lactam ring (Scheme 1). The main methods include the [2 + 2] cycloaddition of acyl ketenes, generated by various methods, with imines [11][12][13][14] and the Wolff rearrangement of γ-amino-α-diazo-β-ketoesters followed by intramolecular
  • cyclization [15][16]. Additionally, the manganese(III)-promoted cyclization of N-alkenyl malonamides [17][18] and the Cu(I)-catalyzed reaction of propiolic acid derivatives with nitrones (Kinugasa reaction) [19][20][21] should also be mentioned, as well as intramolecular C–H insertion using
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Published 05 Aug 2024
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